Chloroacetic Acid → 5-Methoxyuracil

HRID 1362859Notes

Reaction equation

HRID 1362859 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:10])[NH:5][C:6](=S)[NH:7][CH:8]=1.ClCC(O)=[O:14].Cl>O>[CH3:1][O:2][C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:14])[NH:7][CH:8]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 27637595-methoxy-2-sulfanyl-4-pyrimidinol

Product 1

HCID 811005-MethoxyuracilYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(methoxy)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (21.5 g; 0.137 moles), chloroacetic acid (21.5 g; 0.227 moles), and water (585 mL) was refluxed for 2 h. Concentrated HCl (85 mL) was added and the mixture was then refluxed for 16 h. Upon cooling, a solid formed and was collected by filtration, washed with water and dried to yield the desired product (18.2 g; 94% yield). MS: (M+H)+=143.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturethe mixture was then refluxed for 16 h
  3. temperatureUpon cooling
  4. customa solid formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-1b943f1a5cd84fd3835bb57571fc3654
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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